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As a former CEO and founder of OpenTable, I am always trying to learn from our CEOs and other experienced executives how to be a better leader.  I am infinitely curious about leadership, who does it well, what they do and how they engage with their people or customers or investors. It is beautiful when done right. And I find that stoicism and other philosophies are a great tool to use when taking action. Most people assume that philosophy is a passive art that is more about thinking or pondering as you stare off into the distance, theorizing about the perfect action. But that could not be further from the truth. Philosophy is action-oriented. There have been numerous books that have translated the greats (Epictetus, Marcus Aurelius, Seneca,..). And websites like The Daily Stoic put together a list of leaders and popular figures from the past who have been known to practice stoicism. 

Being CEO can be a lonely, difficult job.  And it is a hard job to be in, especially through the different phases of a company’s growth from idea to validation to infrastructure to scale. People who have the kernel of an idea to start a company, are not always the same people that do well at scaling a company. At S2G Ventures we are an entrepreneur-focused fund, working to support the founders and leaders of our portfolio companies as they grow a company through its many phases. Some entrepreneurs, especially most first-time entrepreneurs, don’t understand what scaling a company takes until they experience it. Scale is hard and not many companies figure out how to do it. A lot has to go right. 

S2G’s ethos is to help the entrepreneur continue to develop as a leader who can grow as the company grows. No one is more passionate about an idea than the entrepreneur. No one. However, being a CEO means more than just showing up as the champion of an idea. Our best CEOs are focused on continuous learning and growth. They are deliberate in developing their skills, and few become great leaders through the multiple phases of a company without a lot of hard work. Running a company is not full of glitz and glamor. There are a lot of times where, as an entrepreneur, you are unsure of the next steps, or unsure of the decision that needs to be made because the data is incomplete or counter to your experiences. 

As I evaluate the best CEOs that I have worked within my career, here is what I believe it takes to be a successful, long-term CEO, that scales with a company. And most of these come from the notes or lectures of the great stoic philosophers. 

Get it right, don’t be right. The most important thing (not even a skill) that a CEO can do is to focus on getting it right. Jettison ego. When facing a problem, it shouldn’t matter whose idea it is, only that you get to the best answer. Focus on getting to the right answer for the customer AND the company. To create a learning organization that grows with each decision (big or small) working to get to the right answer should always be goal number one. Most startups are a collection of small wins that build and accelerate on each other over a long period of time, often several years. In the battle for survival, ego more than not, slows a company’s growth, sometimes enough to the point that it can’t break out. Ego destroys value. Create an environment that gets to the right answer, no matter where it comes from. 

Build a (Great) Team. A great CEO surrounds themselves with amazing people. Sometimes a company at an early stage can’t get the world-class talent that they want, but it is critical that the CEO hire people smarter than they are, however and wherever they can. As you are building the business, you need to lead, hire, raise capital, build the product, get customers, create the processes for scale and so many other things that hiring often gets the short end of the deal. A great team allows a CEO to increase their area of influence when they Delegate and Hold Accountable. 

CEO Area of Influence | S2G Ventures Seeding Change

Delegate and Hold Accountable. A “one-person company” or Micro-Manager limits the growth a business can achieve as it builds its products, nurtures its customer base, creates value-added capabilities, and develops new infrastructure in its quest for scale. If the CEO must be part of every decision, a company can never reach its potential. I find that the best leaders set a vision, empower their senior leaders, and remove barriers to their team’s success. The best leaders are not Micro-Managers, they Delegate and Hold Accountable. A CEO who must be part of every decision, keeps their team restrained from doing their best and they can’t cover as much ground or get as much done. Their “Area of Influence” is much smaller. But a CEO that Delegates and Holds Accountable, builds a team that can get a lot more done, much faster. 

Servant Leadership. To many, Servant Leadership doesn’t make sense. If you are the leader, how can you be in service to the people on your team? But to keep your team at its most optimal, removing obstacles in the way of their success, will help them be that much more effective. If you can keep them pushing forward you will be amazed at what a passionate, talented team can get done. Be a force multiplier, by removing obstacles that stand in the way of each of their successes and you will see a lot of successes add up quickly. 

Focus. In my operating past, we called it “maniacal focus.” How can we cut the fat on everything that doesn’t help us execute on a single vision? How can we be the best in the world at one thing? I see very few startups that can grow more than one business at a time, and when I see a lot of revenue lines that need to add up to make a meaningful business, I get concerned. Early on it might be necessary to try a few things to get to Product Market Fit, but great CEOs choose to focus on one thing that will drive value for the business long term.  CEOs want optionality. But with scarce resources, time, and talent, a CEO is usually fighting an entrenched status quo, weary early adopters, and grumpy investors. Which is why, I don’t find optionality to be, well, optimal when starting and building a business. Recently reading Marc Randolf’s book, That Will Never Work, Marc talks about how Netflix was not an online video portal, they were not an online DVD company, they were not an online DVD rental company, they were an online DVD subscription rental company, in the USA. 

Set Objectives and Track Results. I am a huge fan of the OKR (Objective and Key Results) Framework. There are other good goal-setting frameworks out there, but I love the simplicity of OKRs.  John Doerr is one of the leading evangelists out there on OKRs and wrote a great book called Measure What Matters, which gives a practical path to leveraging the superpowers of OKRs. OKRs help make sure the entire team is aligned and rowing in the same direction. They create priorities, remove ambiguity, prioritize the important things and create transparency. And done right, the OKR framework brings the team together as one, in a “get it right” culture. As a team builds out its goal-setting capabilities, the right things get done faster, cheaper and more predictably. 

Take (and seek) Feedback. And while I could probably add a few more, I am going to finish with being a lifelong learner. Learn to keep a beginner’s mind. Inside Amazon, it is not unusual to hear someone say, “everyday is day one,” an expression that Jeff Bezos is credited with starting. It refers to staying hungry, taking chances, learning, taking feedback and not getting caught in the “that’s the way it’s always been done” because nothing has been done before day one. Being open to feedback and a willingness to grow via your team, a professional coach or through honest self-awareness can have powerful returns to a leader’s development. It doesn’t mean that a leader does everything they hear from others. They can’t. Otherwise, they might look like they are watching a ping pong game from the side, back and forth, back and forth. Instead, the key is to hear what others have to say, consider it, weigh the full body of insights and ultimately make a decision. This loops us back to “getting it right.” 

But it’s a two-way street. Just like the CEO needs to commit to their development, we need to be committed to getting better as investors. We need to follow the same set of principles they follow, balancing what we “know” with what we can learn. I consider myself a lifelong practicing stoic, applying it by being a Student of Leadership and Entrepreneurship. I hope to always be learning and strive to put myself into positions in which I can learn and grow as often as possible. What type of action-packed philosophies will you bring to your company?

Philosophy in the Start-Up

Philosophy in the Start-Up


Chuck Templeton

Senior Managing Director

Chuck Templeton is a long-time entrepreneur who has a deep passion for helping early-stage and emerging entrepreneurs and companies scale their businesses. He is focused on helping entrepreneurs use their business innovations to find solutions to the most urgent environmental and societal problems facing humanity today.


Josie Lane

Art Director

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